Iodoethane → 2-Ethyl 6-hydroxybenzo[b]thiophene

HRID 1825228Notes

Reaction equation

HRID 1825228 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[CH:9][S:8][C:7]=2[CH:11]=1.[Li][CH2:13][CH2:14]CC.C(I)C>>[CH2:13]([C:9]1[S:8][C:7]2[CH:11]=[C:3]([OH:2])[CH:4]=[CH:5][C:6]=2[CH:10]=1)[CH3:14]

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 136342376-Methoxy-1-benzothiopheneHCID 178418339Butyllithium

Product 1

HCID 221435082-Ethyl 6-hydroxybenzo[b]thiopheneYield 90%

Procedure

This material was prepared from 6-methoxybenzo[b]thiophene 1a (2.63 g, 16 mmole) by treatment with n-BuLi and ethyl iodide (7.80 g, 50 mmole) in a manner as previously described for example 1b to give a white solid (2.78 g, 90%). 1H NMR (DMSO-d6) δ 7.58 (1H, d, J=8.7 Hz), 7.44 (1H, d, J=2.3 Hz), 7.02 (1H, s), 6.92 (1H, dd, J=2.3, 8.7 Hz), 2.84 (2H, q, J=7.5 Hz), 1.27 (3H, t, J=7.5 Hz).

Sources & evidence

ORD record
ord-048b59a902344b9594dbc721eed1c66e
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

Loading…